Process of making acetophenonphenetidid.



- UNITED STATE R oo s-s o F MAKINGAO-ET Q PHE NQN PHENETiDlQ. I

. To whom.

Beit'known that LFRI DRIO VALENTINER, a subjectof the King otSa'xony, residing at Leipsic-Plagwitz, in the Kingdom of Saxony,,l

Germany,h ave invent-ed certain newiand use- .ful Improvements inPrbcesses for the Red uc tion of Ace'toph'enonphenetidid iuVacuu'm'," (for which Ihave applied for a patent inGermanyNovember 26, 1897,) of

lowing is a specification. 7

My invention relates to an improved process for the production ofacetophenonpheuetidid in vacuum, the rational formula of such substance being as follows The process alreadyknown for the production of acetophenonpheuetidid is based upon the condensation of acetophenone and para phenetidin with the aid of heat. The temperature at which this reaction takes place is from I 1 135 to 140 centigrade-that is, at a temperature at which the paraphenetidiue decomposes in the presence of air and consequently,

causes various discolorations. One of the greatest diffioulties which has to be overcome in carrying out the above-mentioned process is to avoid these decompositions. After the product of the reaction has been cooled the crystallization of the acetophenonphenetidid takes 'placefrom the mother liquor. The wet crystals are then placed upon a suction filter apparatus in order to remove the remaining mother liquor and subsequently washed with alcohol for a'prolonged time. In spite of this complicated and vigorous purification it is still only possible to obtain the acetophenonphenetidid in the state of purity by means of repeated recrystallization from alcohol, ether,

or chloroform. From the mother liquors drawn 06 the acetophenone which had not taken part in the reaction can be recovered for the most part, but the paraphenetidin, on the other hand, cannot be recovered.

The following description sets forth a proc-- ess for the production of acetophenonpheneti-' did in vacuum, which prevents any production of semifluidimpurities andwhich produces by means of a single short operation perfectly-pure; acetophenonphenetidid and at the same time gives back the compounds which the folronjftiming part "of LettrsPatent no; 629,099, dated. July 18,1899. f v A pplicationfiledhpril15,1898. s rum. 577,759. tllospecimensh a I I which have not entered into the reaction in an almost chemically-pure condition.

One-halt kilogram of'acetophenon'e is heated i nan exhaustedretort with one thirty-seventh V of a'kilogram of; paraphenetidin until; there "commences "a" vigorous separation of water.

After this the temperature is allowed to'rise graduallyand thewhole contents of theretort i 'fractionally distilled oif in vacuum. Acetophenone and paraphenetidin' are collected u separately and can be immediately used over again for a fresh charge. At the temperature of 210 to 2l2centigrade and an atmospheric pressure of seventy-two millimeters the acetophenonphenetidid distils and'condenses to a pale-yellow oil,which on cooling solidifies into beautiful clear crystals. A single washing Y I E'RQT0 EI SIQ L GWI Q JGERMANY;

. l p .55 y, Mynewproeess is conducted as.follows:

with alcohol renders the product chemically pure. v

The reactiontakes place according to the following equation:-

The technical advantage .of this process as compared with the previous one is obvious.

The manufacture of the pure "product of the condensation which previously required about a week to prepare each charge can be effected by my new process with the simplest 1 apparatus in four to five hours. The product is of unimpeachable purity, and theyield'is raised from sixty per cent. to about ninetyper cent, and finally the recovered materials which have not entered into combination are practically pure.

'What I claim',anddesire to secure by'Letters Patentof the United States, is V The improved process for the production of acetophenonphenetidid which consists in heating 'acetophe'none and paraphenetidin in molecular proportions in a vacuum to the combination temperatureand distilling ofi therefrom in vacuum the acetophenonphenetidid produced. p In testimony whereof I have hereunto set my hand in the presence of two witnesses.

FRIEDRICH 'VALENTINER.

VVitnessesr 7 RUDOLPH FRIOKE, B. H. WARNER, Jr. 

